Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C12H17NO3 |
Molecular Weight | 223.2683 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]1(O[C@]1([H])C(=O)CC\C=C\C\C=C\C)C(N)=O
InChI
InChIKey=GVEZIHKRYBHEFX-NQQPLRFYSA-N
InChI=1S/C12H17NO3/c1-2-3-4-5-6-7-8-9(14)10-11(16-10)12(13)15/h2-3,5-6,10-11H,4,7-8H2,1H3,(H2,13,15)/b3-2+,6-5+/t10-,11-/m1/s1
DescriptionSources: https://www.drugbank.ca/drugs/DB01034Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21873051 | https://www.ncbi.nlm.nih.gov/pubmed/26005023 | https://www.ncbi.nlm.nih.gov/pubmed/23754252
Sources: https://www.drugbank.ca/drugs/DB01034
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/21873051 | https://www.ncbi.nlm.nih.gov/pubmed/26005023 | https://www.ncbi.nlm.nih.gov/pubmed/23754252
Cerulenin ((2R,3S)-2,3-epoxy-4-oxo-7,10-trans, trans-dodecadienoylamide) is an antifungal antibiotic isolated from Cephalosporium caerulens, that inhibits eukaryotic lipid and sterol synthesis and blocks lipid modification of proteins. Cerulenin is a potent inhibitor of fatty acid synthase (FAS). It inhibits all known types of FASs: both multifunctional enzyme complexes (Type I) (from yeast, rat liver, mammalian cells, and certain bacteria) and unassociated enzymes (Type II) (from most bacteria, and higher plants). Cerulenin blocks the synthesis of polyketides in a wide variety of organisms, including actinomycetes, fungi, and higher plants. In addition, cerulenin is suggested to inhibit the condensation step in polyketide synthesis as well as fatty acid synthesis. Cerulenin has a wide range of antimicrobial activity, the drug significantly inhibits the growth of yeast-like fungi, such as Candida, Saccharomyces, and Cryptococcus. Cerulenin is commercially available as a biochemical reagent for widespread use in the field of obesity, cancer biology, posttranslational protein modification system, drug discovery research and so on.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4158 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21873051 |
5.8 µM [IC50] | ||
Target ID: CHEMBL4530 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26005023 |
4.0 µM [IC50] | ||
Target ID: CHEMBL243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1875332 |
2.5 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
Characterization of N-myristoyl transferase inhibitors and their effect on HIV release. | 1991 Aug |
|
Thiolactomycin resistance in Escherichia coli is associated with the multidrug resistance efflux pump encoded by emrAB. | 1993 Jun |
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Synergistic activities of antituberculous drugs with cerulenin and trans-cinnamic acid against Mycobacterium tuberculosis. | 1998 Jun |
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Antimycobacterial activity of cerulenin and its effects on lipid biosynthesis. | 1999 Feb |
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Cerulenin mimics effects of leptin on metabolic rate, food intake, and body weight independent of the melanocortin system, but unlike leptin, cerulenin fails to block neuroendocrine effects of fasting. | 2001 Apr |
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Inhibition of beta-ketoacyl-acyl carrier protein synthases by thiolactomycin and cerulenin. Structure and mechanism. | 2001 Mar 2 |
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Fatty acid synthase inhibition results in a magnetic resonance-detectable drop in phosphocholine. | 2008 Aug |
|
Chemical genetic profiling and characterization of small-molecule compounds that affect the biosynthesis of unsaturated fatty acids in Candida albicans. | 2009 Jul 17 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23754252
SCID mice were treated with Cerulenin 15 and 30 mg/kg every 3 days
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23754252
To measure the cytotoxicity of cerulenin against HCT116 and RKO cells, 3x103 cells were plated per well onto 96-well plates. Following overnight culture, cerulenin and oxaliplatin were added at specified concentra¬tions. After 24 h of incubation, cell viability was measured by the mitochondrial activity in reducing 2-(2-methoxy-4-nitrophenyl)-3-(4-nitrophenyl)-5-(2,4-disulfophenyl)-2H-tetra¬zolium monosodium salt (WST-8) to formazan using a Cell Counting kit-8 (Dojindo Laboratories, Kumamoto, Japan). Cells were incubated with a reagent according to the manufac¬turer's instructions. Plates were read at A450 on a spectrometer.
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116069
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241-424-8
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DB01034
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578
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MF286Y830Q
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Cerulenin
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17397-89-6
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171741
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5282054
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DTXSID2040995
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m3273
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PRIMARY | Merck Index |
SUBSTANCE RECORD